4,7-Dibromo-N-methoxy-N-methyl-2,3-dihydro-1H-indene-5-carboxamide → (4,7-Dibromo-2,3-dihydro-1H-inden-5-yl)(4-ethylphenyl)methanone

HRID 2206673노트

반응식

HRID 2206673 반응식
[Br:1][C:2]1[C:10]([C:11](N(OC)C)=[O:12])=[CH:9][C:8]([Br:17])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2.[CH2:18]([C:20]1[CH:25]=[CH:24][C:23]([Mg]Br)=[CH:22][CH:21]=1)[CH3:19]>C1COCC1>[Br:1][C:2]1[C:10]([C:11]([C:23]2[CH:24]=[CH:25][C:20]([CH2:18][CH3:19])=[CH:21][CH:22]=2)=[O:12])=[CH:9][C:8]([Br:17])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2

참가 물질

4

반응물 2

HCID 867140174,7-Dibromo-N-methoxy-N-methyl-2,3-dihydro-1H-indene-5-carboxamideHCID 178436501HCID 178436501, 화합물

생성물 1

HCID 71110539(4,7-Dibromo-2,3-dihydro-1H-inden-5-yl)(4-ethylphenyl)methanone수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of amide 9 (0.27 g, 0.73 mmol) in anhydrous THF (2.7 mL) was added dropwise 4-ethylphenylmagnesium bromide (3.65 mL of 0.5 M in THF, 1.83 mol) at 0° C. under nitrogen atmosphere. The mixture was warmed up to room temperature slowly and stirred at room temperature for 15 h. The reaction mixture was quenched with 1 M HCl solution (10 mL) and extracted with EtOAc (20 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the compound 10 (0.25 g, 0.62 mmol, 85%).

후처리

  1. customThe reaction mixture was quenched with 1 M HCl solution (10 mL)
  2. extractionextracted with EtOAc (20 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bd44af28324f438aa1b70c39927358cd
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371303B2

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